6-fluoro-1-methyl-1H-indole-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-fluoro-1-methyl-1H-indole-3-carbonitrile
• 英文别名: 6-Fluoro-1-methylindole-3-carbonitrile；6-fluoro-1-methylindole-3-carbonitrile
• 化学式: C₁₀H₇FN₂
• 分子量: 174.177
• InChiKey: FMUPRGQQCYUOHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-氟-1-甲基-1H-吲哚-3-甲醛 在 吡啶 、 selenium(IV) oxide 、 盐酸羟胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 6-fluoro-1-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Probing the phytopathogenic stem rot fungus with phytoalexins and analogues: unprecedented glucosylation of camalexin and 6-methoxycamalexin

  摘要：

  The remarkable metabolism of the cruciferous phytoalexins camalexin and 6-methoxycamalexin by the stem rot phytopathogen Sclerotinia sclerotiorum is reported. The biotransformations yielded camalexins glucosylated at N-1 or C-6 of the indole ring, with substantially lower antifungal activity than camalexins. A camalexin analogue with the positions N-1 and C-6 blocked was metabolized but at a much slower rate than the natural phytoalexins. The chemistry involved in the metabolism of natural camalexins and two new analogues, as well as their novel metabolites and respective antifungal activities is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00208-0

文献信息

• Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium
  作者：Bin Liu、Jiehui Wang、Bo Zhang、Yang Sun、Lei Wang、Jianbin Chen、Jiang Cheng

  DOI：10.1039/c3cc49339c

  日期：——

  A copper-promoted C3-cyanation of both the free N–H and N-protected indoles by N,N,N′,N′-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O followed by hydrolyzation to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O2 as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles.

  通过 N,N,N′,N′-四甲基乙烷-1,2-二胺（TMEDA）和铵的促进，铜催化的 C3-氰化反应成功实现了游离 N–H 和 N-保护吲哚的氰化。亚胺离子作为该转化过程中的中间体，依次受到吲哚和 H2O 的亲电攻击，然后水解形成醛。接着，醛与铵的反应生成腈。这一反应采用 O2 作为清洁氧化剂，具有良好的效率和官能团耐受性。因此，它代表了一种简便且安全的步骤，能够产生 3-氰吲哚。
• Palladium-Catalyzed Directed Carbon–Carbon Bond Activation of Aryl Nitriles for Cyano Transfer
  作者：Lin Tan、Yang Pan、Qing-Ying Zeng、Zhen-Yu Wang、Hui Xu、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.4c00429

  日期：2024.3.22

  Herein, we report the C–H cyanation of indoles via a palladium-catalyzed directed C–CN activation reaction using aryl nitrile as a cyano source. The employment of the phenoxy-oriented group is the key to the cleavage of the C–CN bond. This protocol features a broad substrate scope, good efficiency, and high regioselectivity. Furthermore, the practical application of this protocol was showcased in the

  在此，我们报道了使用芳基腈作为氰基源，通过钯催化的定向 C-CN 活化反应进行吲哚的 C-H 氰化。苯氧基取向基团的使用是C-CN键断裂的关键。该方案具有底物范围广、效率高、区域选择性高的特点。此外，该方案的实际应用在吲哚衍生物的后期功能化和合成中得到了展示，吲哚衍生物是通过氰化过程衍生自药物和天然产物。
• Probing the phytopathogenic stem rot fungus with phytoalexins and analogues: unprecedented glucosylation of camalexin and 6-methoxycamalexin
  作者：M Pedras

  DOI：10.1016/s0968-0896(02)00208-0

  日期：2002.10

  The remarkable metabolism of the cruciferous phytoalexins camalexin and 6-methoxycamalexin by the stem rot phytopathogen Sclerotinia sclerotiorum is reported. The biotransformations yielded camalexins glucosylated at N-1 or C-6 of the indole ring, with substantially lower antifungal activity than camalexins. A camalexin analogue with the positions N-1 and C-6 blocked was metabolized but at a much slower rate than the natural phytoalexins. The chemistry involved in the metabolism of natural camalexins and two new analogues, as well as their novel metabolites and respective antifungal activities is described. (C) 2002 Elsevier Science Ltd. All rights reserved.